A hydroxyphenylpropionamide benzoic acid silanol composition, method of making and use thereof

Abstract

The application discloses a hydroxyphenylpropionamide benzoic acid silanol composition, a preparation method and application thereof, and belongs to the technical field of new fine chemical materials. The composition is formed by using water and a diol solvent as a mixed system of a solvent medium, using hydroxyphenylpropionamide benzoic acid as a silanol system stabilizer, and then being compounded with active silanol derivatives, pH being regulated, and being stirred and reacted to form a stable silanol active composition; the method is characterized in that a multi-molecular small-molecule organosilanol is stably arranged in a stable supramolecular system which is jointly constructed by the organosilanol system stabilizer hydroxyphenylpropionamide benzoic acid and water and a diol solvent, and the stereospecific protection system at the molecular level can fix the active silanol in the solution, reduce the condensation of the active silanol in the water solution, and enable the skin to effectively absorb the active silanol; the method can improve the solubility, thermal stability and other physical and chemical properties of hydroxyphenylpropionamide benzoic acid, and achieve better comprehensive effects such as soothing, moisturizing and anti-wrinkling.

Description

Technical Field

[0001] This invention relates to the field of fine chemical new materials technology, and more specifically to a hydroxyphenylpropionamide benzoic acid silanol composition, its preparation method and its application. Background Technology

[0002] Hydroxyphenylpropionamide benzoic acid, as a highly effective non-steroidal anti-inflammatory agent, can exert anti-inflammatory, antihistamine, soothing, and erythema-improving effects by inhibiting the histamine signaling pathway, and is widely used in sensitive skin care products. However, its poor water solubility and limited transdermal absorption efficiency, as well as its susceptibility to oxidation and deterioration when exposed to light and heat, limit its full potential.

[0003] Silanols have the effects of promoting collagen production, repairing connective tissue, and delaying skin aging. From a skin physiology perspective, inflammation is closely related to aging, a phenomenon known as "inflammatory aging." Theoretically, combining hydroxyphenylpropionamide benzoic acid with silanols can achieve a dual synergistic effect of anti-inflammatory soothing and anti-aging. However, the common shortcomings of the aforementioned active substances, such as poor stability, low bioavailability, difficulty in formulation, or irritation, severely limit their high-value applications. Summary of the Invention

[0004] In view of this, the present invention provides a hydroxyphenylpropionamide benzoic acid silanol composition, a preparation method thereof, and its application. The composition has strong stability, high bioavailability, no / low irritation, and good transdermal absorption, which can solve the bottleneck problems existing in the prior art.

[0005] To achieve the above objectives, the present invention adopts the following technical solution.

[0006] On the one hand, the present invention proposes a hydroxyphenylpropionamide benzoic acid silanol composition, the general structural formula of which is shown below:

[0007]

[0008] Wherein: group R1 is one of the following: straight-chain or branched alkoxy or unsaturated hydrocarbon or unsaturated alkynyl group -OC1-C4, -OCH3CHOH, -OCH2OH, straight-chain or branched C1-C4 alkyl or unsaturated hydrocarbon group, unsaturated alkynyl group;

[0009] The group R2 is one of -NH2, -H, -OH, -OCH2OH, -OCH2CH2OH, straight-chain C1-C2 alkyl or unsaturated hydrocarbon group and unsaturated alkynyl group.

[0010] Secondly, the present invention provides a method for preparing a hydroxyphenylpropionamide benzoic acid silanol composition, comprising the following steps:

[0011] (1) Take water and glycol solvent in proportion, and stir them thoroughly at 25-60℃ for 5-10 min to obtain a mixed solvent medium system;

[0012] (2) Add hydroxyphenylpropionamide benzoic acid, a silanol system stabilizer, to the mixed solvent medium system, and sonicate for 10-30 min to obtain a uniform dispersion;

[0013] (3) Under argon protection, add the active silanol derivative dropwise to the uniform dispersion, stir at 25-60℃ for 20-30 min, adjust the pH value to 5.5-7, and maintain the reaction at 25-60℃ for 1-3 hours to obtain a hydroxyphenylpropionamide benzoic acid silanol mixture.

[0014] (4) After filtering out insoluble impurities and distilling under reduced pressure, a hydroxyphenylpropionamide benzoic acid silanol composition is obtained.

[0015] In the preparation method of the above-mentioned hydroxyphenylpropionamide benzoic acid silanol composition, the diol solvent is one or more of propylene glycol, butanediol, methylpropanediol, pentanediol, and hexanediol.

[0016] In the preparation method of the above-mentioned hydroxyphenylpropionamide benzoic acid silanol composition, the active silanol derivative is used in an amount of 0.1-2% by mass percentage, the hydroxyphenylpropionamide benzoic acid is used in an amount of 0.1-5%, and the balance is a mixed solvent medium system of water and glycol solvent.

[0017] In the above-mentioned hydroxyphenylpropionamide benzoic acid silanol composition, the ratio of water to diol solvent is (4:1) to (2:1).

[0018] The method for preparing the above-mentioned hydroxyphenylpropionamide benzoic acid silanol composition, wherein the general structural formula of the active silanol derivative is shown below,

[0019]

[0020] Wherein: group R1 is one of the following: straight-chain or branched alkoxy or unsaturated hydrocarbon or unsaturated alkynyl group -OC1-C4, -OCH3CHOH, -OCH2OH, straight-chain or branched C1-C4 alkyl or unsaturated hydrocarbon group, unsaturated alkynyl group;

[0021] The group R2 is one of -Cl, -H, -NH2, -OCH2OH, -OCH2CH2OH, straight-chain C1-C2 alkyl or unsaturated hydrocarbon group and unsaturated alkynyl group.

[0022] The stabilizer for the silanol system is hydroxyphenylpropionamide benzoic acid, which can form at least one hydrogen bond or a complex with the final silanol system and the solvent medium of water and glycol solvent, thus constructing a stable supramolecular interaction system.

[0023] In the solvent medium of this invention, the ratio of water to alcohol is crucial. Too much water can easily cause silanol condensation and precipitation of hydroxyphenylpropionamide benzoic acid, resulting in turbidity and instability, which is detrimental to the stability of subsequent application products.

[0024] Thirdly, the present invention proposes the application of a hydroxyphenylpropionamide benzoic acid silanol composition in skin care products.

[0025] This invention stabilizes multi-molecule organosilanols in a stable supramolecular system composed of organosilanol stabilizer hydroxyphenylpropionamide benzoic acid, water, and glycol solvent. This molecular-level stereoactive protective system can significantly fix the active silanols in the solution, reducing their tendency to condense easily in aqueous solutions, which would prevent effective absorption by the skin and thus reduce their loss of biological activity.

[0026] This invention enhances the supramolecular forces of multiple small-molecule organosilicones by superimposing them, thereby increasing the interaction forces between the supramolecular hydrogen bond network system. By combining amphiphilic (hydrophilic and lipophilic) small-molecule organosilicones, this invention achieves a better effect in improving the solubility of organosilicone system stabilizers, transforming active substances that are originally difficult to dissolve in water or alcohols in cosmetics into water-soluble and alcohol-soluble systems, making them suitable for more formulation systems such as serums, creams, and lotions. Through silanization, leveraging the high compatibility between hydroxyl and amino groups on active molecules and silanol groups, a hydrogen-bonded spatial network system with stronger interactions than ordinary hydroxyl groups is constructed. This enhances the stability and controlled-release capability of the active ingredient, addressing several pain points: hydroxyphenylpropionamide benzoic acid, being a thermosensitive, photosensitizing, and oxygen-sensitive molecule, is prone to irreversible degradation or configurational changes; the active sites for reaction between active molecules and organosilanols are limited; simple blending has poor compatibility, preventing the formation of a long-term stable homogeneous system; and active substances are prone to precipitation, degradation, and slow self-polymerization during storage. This approach balances the integrity of the active ingredient structure, stable binding with high loading capacity, and long-term storage stability of the composition. By incorporating a skin-friendly small-molecule silanol system, the transdermal penetration and retention of active ingredients are significantly improved, increasing bioavailability and allowing the active ingredient to reach its target more effectively, further enhancing antihistamine efficacy. Attached Figure Description

[0027] Figure 1a This is a liquid chromatogram of the transdermal absorption acceptor solution of the hydroxyphenylpropionamide benzoic acid silanol solution of the present invention; Figure 1bThe liquid chromatogram of the transdermal absorption acceptor solution of hydroxyphenylpropionamide benzoic acid alcohol solution; Figure 1c The liquid chromatogram of the transdermal absorption acceptor solution of hydroxyphenylpropionamide benzoic acid (potassium salt) aqueous solution;

[0028] Figure 2a This is a liquid chromatogram of the hydroxyphenylpropionamide benzoic acid silanol solution absorbed through the epidermal layer in this invention. Figure 2b The image shows a liquid chromatogram of a hydroxyphenylpropionamide benzoic acid alcohol solution absorbed through the epidermal layer. Figure 2c The image shows a liquid chromatogram of the epidermal layer absorbed from an aqueous solution of hydroxyphenylpropionamide benzoic acid (potassium salt).

[0029] Figure 3a This is a liquid chromatogram of the dermal layer absorbed through the transdermal layer by the hydroxyphenylpropionamide benzoic acid silanol solution of the present invention; Figure 3b The chromatogram of hydroxyphenylpropionamide benzoic acid alcohol solution absorbed through the dermal layer by liquid chromatography. Figure 3c The chromatogram of dermal liquid chromatography obtained by transdermal absorption of an aqueous solution of hydroxyphenylpropionamide benzoic acid (potassium salt);

[0030] Figure 4 This is a comparative diagram of the thermal acceleration experiments of the hydroxyphenylpropionamide benzoic acid silanol solution and the hydroxyphenylpropionamide benzoic acid solution of the present invention;

[0031] Figure 5 This is a comparison diagram of the antihistamine experiments of zebrafish in Example 4 with those in Comparative Examples 1 and 2. Detailed Implementation

[0032] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0033] This invention discloses a hydroxyphenylpropionamide benzoic acid silanol composition, the general structural formula of which is shown below.

[0034]

[0035] In the formula: group R1 is one of the following: straight-chain or branched alkoxy or unsaturated hydrocarbon or unsaturated alkynyl group -OC1-C4, -OCH3CHOH, -OCH2OH, straight-chain or branched C1-C4 alkyl or unsaturated hydrocarbon group, and unsaturated alkynyl group;

[0036] The group R2 is one of -NH2, -H, -OH, -OCH2OH, -OCH2CH2OH, straight-chain C1-C2 alkyl or unsaturated hydrocarbon group and unsaturated alkynyl group.

[0037] Its preparation method includes the following steps:

[0038] (1) Take water and glycol solvent in proportion, and stir them thoroughly at 25-60℃ for 5-10 min to obtain a mixed solvent medium system;

[0039] (2) Add hydroxyphenylpropionamide benzoic acid, a silanol system stabilizer, to the mixed solvent medium system, and sonicate for 10-30 min to obtain a uniform dispersion;

[0040] (3) Under argon protection, add the active silanol derivative dropwise to the uniform dispersion, stir at 25-60℃ for 20-30 min, adjust the pH value to 5.5-7, and maintain the reaction at 25-60℃ for 1-3 hours to obtain a hydroxyphenylpropionamide benzoic acid silanol mixture.

[0041] The active silanol derivatives have the following general structural formula:

[0042]

[0043] Wherein: group R1 is one of the following: straight-chain or branched alkoxy or unsaturated hydrocarbon or unsaturated alkynyl group -OC1-C4, -OCH3CHOH, -OCH2OH, straight-chain or branched C1-C4 alkyl or unsaturated hydrocarbon group, unsaturated alkynyl group;

[0044] The group R2 is one of -Cl, -H, -NH2, -OCH2OH, -OCH2CH2OH, straight-chain C1-C2 alkyl or unsaturated hydrocarbon group and unsaturated alkynyl group.

[0045] (4) After filtering out insoluble impurities and distilling under reduced pressure, a hydroxyphenylpropionamide benzoic acid silanol composition is obtained.

[0046] The following will verify the preparation process and effects of the hydroxyphenylpropionamide benzoic acid silanol composition prepared according to the present invention with reference to specific embodiments.

[0047] Example 1: This example describes the preparation of a hydroxyphenylpropionamide benzoic acid silanol composition, the preparation method of which includes the following steps:

[0048] (1) Take 153g of ultrapure water, 40g of methyl propylene glycol and 20g of propylene glycol and mix them thoroughly at 25℃ for 10min to obtain a mixed solvent;

[0049] (2) Take 6.0g of organosilanol stabilizer hydroxyphenylpropionamide benzoic acid and slowly add it to the above mixed solvent, and ultrasonically disperse for 15min;

[0050] (3) Under argon protection, 1 g of trichloromethylsilane was added dropwise to the above hydrochlorophenyl propionamide benzoic acid aqueous alcohol solution at a rate of 0.8 mL / min, the temperature was controlled at 25℃, and after stirring for 30 min, 0.1 mol / L sodium hydroxide solution was added dropwise at a rate of 0.5 mL / min, the pH was maintained at 5.5-7, and stirring was continued for 2 hours to obtain a hydrochlorophenyl propionamide benzoic acid silanol mixture;

[0051] (4) Filter out insoluble impurities and concentrate under reduced pressure at 40℃ and -0.095MPa to 100g to obtain a colorless and transparent hydroxyphenylpropionamide benzoic acid silanol composition.

[0052] Example 2: This example describes the preparation of a hydroxyphenylpropionamide benzoic acid silanol composition, the preparation method of which includes the following steps:

[0053] (1) Take 153g of ultrapure water, 40g of methyl propylene glycol and 20g of propylene glycol and mix them thoroughly at 25℃ for 10min to obtain a mixed solvent;

[0054] (2) Take 6.0g of organosilanol stabilizer hydroxyphenylpropionamide benzoic acid and slowly add it to the above mixed solvent, and ultrasonically disperse for 15min;

[0055] (3) Under argon protection, 1 g of vinyltrichlorosilane was added dropwise to the above hydroxyphenylpropionamide benzoic acid aqueous alcohol solution at a rate of 0.8 mL / min, the temperature was controlled at 25 °C, and the mixture was stirred for 30 min. 0.1 mol / L sodium hydroxide solution was added dropwise at a rate of 0.5 mL / min, the pH was kept at 5.5-7, and the mixture was stirred for 2 hours to obtain a hydroxyphenylpropionamide benzoic acid silanol mixture.

[0056] (4) Filter out insoluble impurities and concentrate under reduced pressure at 40℃ and -0.095MPa to 100g to obtain a colorless and transparent hydroxyphenylpropionamide benzoic acid silanol composition.

[0057] Example 3: This example describes the preparation of a hydroxyphenylpropionamide benzoic acid silanol composition, using the following steps:

[0058] (1) Take 153g of ultrapure water, 40g of methyl propylene glycol and 20g of propylene glycol and mix them thoroughly at 25℃ for 10min to obtain a mixed solvent;

[0059] (2) Take 6.0g of organosilanol stabilizer hydroxyphenylpropionamide benzoic acid and slowly add it to the above mixed solvent, and ultrasonically disperse for 15min;

[0060] (3) Under argon protection, 1 g of dimethoxydichlorosilane was added dropwise to the above hydroxyphenylpropionamide benzoic acid aqueous alcohol solution at a rate of 0.8 mL / min, the temperature was controlled at 10-20℃, and 0.1 mol / L sodium hydroxide solution was added dropwise at a rate of 0.5 mL / min, the pH was maintained at 5.5-6, and the mixture was stirred for 2 hours to obtain a hydroxyphenylpropionamide benzoic acid silanol mixture.

[0061] (4) Filter out insoluble impurities, and evaporate at 50℃ and -0.095MPa. Concentrate under reduced pressure to 100g to obtain a colorless and transparent hydroxyphenylpropionamide benzoic acid silanol composition.

[0062] Example 4: In this example, a soothing serum containing the hydroxyphenylpropionamide benzoate silanol composition prepared in Example 1 was prepared. The percentage of each component in the serum (by mass fraction) is shown in Table 1 below.

[0063]

[0064] The preparation process is as follows:

[0065] S1. Raw material pretreatment:

[0066] a) Mix the three thickeners in phase B thoroughly and pass them through an 80-mesh sieve;

[0067] b) Dissolve the C-phase arginine in 50g of deionized water to form a clear solution for later use;

[0068] S2. Preparation process:

[0069] a) Add the remaining 7797g water, 5g disodium EDTA, 200g butanediol, 50g p-hydroxyacetophenone, and 50g hexanediol to an emulsifying pot, heat to 75-80℃ while stirring at low speed (30-40 rpm), and keep warm and stirring for 10 minutes until completely dissolved.

[0070] b) Add the sieved B phase to 100g of butanediol and stir at high speed (800-1000rpm) for 5min until a uniform paste without dry powder or lumps is formed.

[0071] c) Add the dissolved B phase to the A phase and homogenize (2000 rpm) for 3 min, then stir at medium speed (40 rpm) and keep warm for 15 min until the thickener is completely swollen and the system is a uniform, transparent, thin gel.

[0072] d) Cool to below 45°C, add phase C arginine solution, and stir (40 rpm) for 15 min;

[0073] e) Cool down to below 40°C, add 1650g of the hydroxyphenylpropionamide benzoic acid silanol composition (D phase) and stir at low speed (20 rpm) for 15 minutes until completely mixed;

[0074] f) Turn on the vacuum system (-0.06~-0.08MPa), stir at low speed for 15 minutes to remove bubbles from the system, and obtain the essence containing the hydroxyphenylpropionamide benzoic acid silanol composition.

[0075] Comparative Example 1: In this example, a soothing serum containing 3% alcohol-soluble hydroxyphenylpropionamide benzoic acid was prepared. The proportions of each group are shown in Table 2 below.

[0076]

[0077] The specific preparation process is the same as in Example 4.

[0078] Comparative Example 2: In this example, a soothing serum containing 3% water-soluble hydroxyphenylpropionamide benzoic acid (potassium salt) was prepared. The composition of each group is shown in Table 3 below.

[0079]

[0080] The specific preparation process is the same as in Example 4.

[0081] Test Example 1: Soothing Performance Test of Hydroxyphenylpropionamide Benzoic Acid Silanol Composition

[0082] Test method:

[0083] (1) Take 0.5 mL of the sample solution of Example 1, Example 2 and Example 3 after dilution to a content of 0.5%, and prepare ordinary 0.5% hydroxyphenylpropionamide benzoic acid alcohol solution (positive control group 1) and 0.5% hydroxyphenylpropionamide benzoic acid (potassium salt) aqueous solution (positive control group 2), respectively, add 0.5 mL of hyaluronidase solution with a concentration of 500 U / mL to each, and incubate at 37℃ for 20 min;

[0084] (2) Add 0.1 mL of CaCl2 solution and incubate at 37 °C for 20 min;

[0085] (3) Add 0.5 mL of sodium hyaluronate solution, keep at 37°C for 40 min, and then let stand at room temperature for 10 min;

[0086] (4) Add 0.5 mL of distilled water, 0.1 mL of NaOH solution and 0.5 mL of acetylacetone solution, heat in boiling water for 15 min, remove and cool with ice water for 10 min;

[0087] (5) Prepare 1.0 mL of DAB horseradish peroxidase colorimetric reagent, shake each test tube thoroughly, add anhydrous ethanol to 8 mL, and let stand at room temperature for 30 min; (6) Add and measure absorbance at 530 nm.

[0088] Evaluation criteria: Inhibition rate ≥70% indicates strong anti-inflammatory and anti-allergic effect; ≥50% indicates moderate anti-inflammatory and anti-allergic effect; ≥30% indicates weak anti-inflammatory and anti-allergic effect; <30% indicates no anti-inflammatory and anti-allergic effect. The hyaluronidase inhibition rate results for different treatment groups are shown in Table 4 below.

[0089]

[0090] As can be seen from Table 4, the silanol complex treatment significantly enhanced the inhibitory activity of hydroxyphenylpropionamide benzoic acid on hyaluronidase, and the combination pathway in Example 1 showed the highest inhibitory and soothing effect.

[0091] Experimental Example 2: Transdermal Absorption Test

[0092] Phosphate-buffered saline (PBS) treated pigskin was mixed with a certain amount of Tween 80 to a mass fraction of 5%, and placed in a receiving cell. 0.5 mL each of the sample solution from Example 1 and the diluted 0.5% solution, as well as 0.5 mL of a common 0.5% hydroxyphenylpropionamide benzoic acid alcohol solution (positive control group 1) and a 0.5% hydroxyphenylpropionamide benzoic acid (potassium salt) aqueous solution (positive control group 2), were added. The Franz diffusion cell was then placed in a transdermal diffusion apparatus, with the experimental temperature set at 37°C, the stirring speed at 600 rpm, and the reaction time at 12 h. After the reaction, the hydroxyphenylpropionamide benzoic acid content in the treated pigskin was determined by HPLC, representing the hydroxyphenylpropionamide benzoic acid content in the epidermis and dermis, to reflect the system's penetration effect. The permeability was calculated 24 h after transdermal absorption using the following formula:

[0093] Permeability = Content of the layer / Theoretical content of the sample * 100%.

[0094] The results are shown in Figures 1-3 and Table 5 below; where Figure 1a This is a liquid chromatogram of the transdermal absorption acceptor solution of the hydroxyphenylpropionamide benzoic acid silanol solution of the present invention; Figure 1b The liquid chromatogram of the transdermal absorption acceptor solution of hydroxyphenylpropionamide benzoic acid alcohol solution; Figure 1c The liquid chromatogram of the transdermal absorption acceptor solution of hydroxyphenylpropionamide benzoic acid (potassium salt) aqueous solution; Figure 2a This is a liquid chromatogram of the hydroxyphenylpropionamide benzoic acid silanol solution absorbed through the epidermal layer in this invention. Figure 2b The image shows a liquid chromatogram of a hydroxyphenylpropionamide benzoic acid alcohol solution absorbed through the epidermal layer. Figure 2cThe image shows a liquid chromatogram of the epidermal layer absorbed from an aqueous solution of hydroxyphenylpropionamide benzoic acid (potassium salt). Figure 3a This is a liquid chromatogram of the dermal layer absorbed through the transdermal layer by the hydroxyphenylpropionamide benzoic acid silanol solution of the present invention; Figure 3b The chromatogram of hydroxyphenylpropionamide benzoic acid alcohol solution absorbed through the dermal layer by liquid chromatography. Figure 3c This is a chromatogram of the dermal layer obtained by transdermal absorption of an aqueous solution of hydroxyphenylpropionamide benzoic acid (potassium salt).

[0095]

[0096] Combined with Table 5 and Figures 1a-1c It can be seen that the average permeability of Example 1, Positive 1 (alcohol-soluble), and Positive 2 (water-soluble) are 0.059, 0.006, and 0.13, respectively. Comparing Positive 2 with Positive 1, it can be seen that the transdermal permeability of hydroxyphenylpropionamide benzoic acid is significantly enhanced after the water solubility is enhanced. However, cosmetic active ingredients need to be kept in the skin, that is, absorbed through the skin. The hydroxyphenylpropionamide benzoic acid in Example 1 is amphiphilic (hydrophilic and lipophilic), which can significantly reduce the problem of excessive permeation caused by strong water solubility.

[0097] Combined with Table 5 and Figures 2a-2c As shown in 3a-3c, in the epidermis, the average permeability of Example 1, Positive 1 (alcohol-soluble), and Positive 2 (water-soluble) were 0.58, 0.13, and 0.37, respectively; while in the dermis, the average permeability of Example 1, Positive 1 (alcohol-soluble), and Positive 2 (water-soluble) were 0.58, 0.13, and 0.37, respectively. It can be seen that the silanol compound treatment can significantly increase the permeation and retention of hydroxyphenylpropionamide benzoic acid, and both are superior to water-soluble and alcohol-soluble hydroxyphenylpropionamide benzoic acid. It can better inhibit the inflammation and allergic reactions caused by hyaluronidase and mast cells (releasing histamine) located in the epidermis and dermis.

[0098] Experiment 3: Stability Test

[0099] The hydroxyphenylpropionamide benzoic acid silanol composition prepared in Example 1 was stored with water-soluble hydroxyphenylpropionamide benzoic acid (potassium salt) (positive control 1) in a 45°C accelerated thermal aging test chamber for 120 days. The retention rate was detected by high-performance liquid chromatography (HPLC); simultaneously, the system was observed for discoloration and odor development. Results are as follows... Figure 4 As shown in Table 6 below.

[0100]

[0101] As shown in Table 6 above Figure 4As shown, after a 120-day stability test, it can be seen that the content and color of the hydroxyphenylpropionamide benzoic acid silanol composition prepared in Example 1 did not change, while the content and color of the water-soluble hydroxyphenylpropionamide benzoic acid (potassium salt) both changed. This indicates that the stability of the hydroxyphenylpropionamide benzoic acid silanol composition prepared in this invention is significantly higher than that of ordinary hydroxyphenylpropionamide benzoic acid solution.

[0102] Experiment 4: Serum Soothing Performance Test (Histamine Inhibition Rate Test Method (Zebrafish Test))

[0103] Zebrafish were randomly selected and placed in 6-well plates, 30 fish per well. They were given the aqueous extracts of Examples 4, 1, and 2 (Comparative Example 1 and 2). A normal control group and a model control group were also included. Each well contained 3 mL of extract. Except for the normal control group, all other experimental groups were given C48 / 80 aqueously to establish a zebrafish allergy model. The experimental procedures were biologically replicated three times. Each experimental group was incubated in the dark for 24 h. After collection, the samples were homogenized using a grinder, centrifuged, and the supernatant was collected. Histamine content was measured using a fish histamine (HIS) kit to calculate the histamine inhibition rate of the three extracts and evaluate the soothing effect. The results are as follows: Figure 5 As shown in Table 7 below.

[0104]

[0105] From Table 7 and Figure 5 It can be seen that, with other ingredients and preparation processes remaining unchanged, the soothing serum containing the hydroxyphenylpropionamide benzoic acid silanol composition of the present invention prepared in Example 4 has a significantly higher histamine inhibition rate than Comparative Example 1 (soothing serum containing 3% alcohol-soluble hydroxyphenylpropionamide benzoic acid) and Comparative Example 2 (soothing serum containing 3% water-soluble hydroxyphenylpropionamide benzoic acid (potassium salt)). This indicates that the hydroxyphenylpropionamide benzoic acid silanol composition prepared in the present invention can significantly promote the histamine inhibition effect and give the serum a better soothing and anti-allergic effect.

[0106] Similar or identical parts between the various embodiments in this specification can be referred to mutually. The above description of the disclosed embodiments enables those skilled in the art to make or use the invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the invention. Therefore, the invention is not to be limited to the embodiments shown herein, but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. A hydroxyphenylpropionamide benzoic acid silanol composition, characterized in that, The general structural formula is as follows: Wherein: group R1 is one of the following: straight-chain or branched alkoxy or unsaturated hydrocarbon or unsaturated alkynyl group -OC1-C4, -OCH3CHOH, -OCH2OH, straight-chain or branched C1-C4 alkyl or unsaturated hydrocarbon group, unsaturated alkynyl group; The group R2 is one of -NH2, -H, -OH, -OCH2OH, -OCH2CH2OH, straight-chain C1-C2 alkyl or unsaturated hydrocarbon group and unsaturated alkynyl group.

2. The method for preparing the hydroxyphenylpropionamide benzoic acid silanol composition according to claim 1, characterized in that, Includes the following steps: (1) Take water and glycol solvent in proportion, and stir them thoroughly at 25-60℃ for 5-10 min to obtain a mixed solvent medium system; (2) Add hydroxyphenylpropionamide benzoic acid, a silanol system stabilizer, to the mixed solvent medium system, and sonicate for 10-30 min to obtain a uniform dispersion; (3) Under argon protection, add the active silanol derivative dropwise to the uniform dispersion, stir at 25-60℃ for 20-30 min, adjust the pH value to 5.5-7, and maintain the reaction at 25-60℃ for 1-3 hours to obtain a hydroxyphenylpropionamide benzoic acid silanol mixture. (4) After filtering out insoluble impurities and distilling under reduced pressure, a hydroxyphenylpropionamide benzoic acid silanol composition is obtained.

3. The method for preparing the hydroxyphenylpropionamide benzoic acid silanol composition according to claim 2, characterized in that, The diol solvent is one or more of propylene glycol, butanediol, methylpropylene glycol, pentanediol, and hexanediol.

4. The method for preparing the hydroxyphenylpropionamide benzoic acid silanol composition according to claim 2, characterized in that, The active silanol derivative is used in an amount of 0.1-2% by mass, the hydroxyphenylpropionamide benzoic acid is used in an amount of 0.1-5%, and the balance is a mixed solvent medium system of water and glycol solvent.

5. The hydroxyphenylpropionamide benzoate silanol composition according to claim 4, characterized in that, The ratio of water to glycol solvent is (4:1) to (2:1).

6. The method for preparing the hydroxyphenylpropionamide benzoic acid silanol composition according to claim 2, characterized in that, The general structural formula of the active silanol derivative is shown below. Wherein: group R1 is one of the following: straight-chain or branched alkoxy or unsaturated hydrocarbon or unsaturated alkynyl group -OC1-C4, -OCH3CHOH, -OCH2OH, straight-chain or branched C1-C4 alkyl or unsaturated hydrocarbon group, unsaturated alkynyl group; The group R2 is one of -Cl, -H, -NH2, -OCH2OH, -OCH2CH2OH, straight-chain C1-C2 alkyl or unsaturated hydrocarbon group and unsaturated alkynyl group.

7. The use of the hydroxyphenylpropionamide benzoate silanol composition as described in claim 1 in the preparation of skin care products.

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